Gossypol

Gossypol is a lipid of Prenol Lipids (PR) class. Gossypol is associated with abnormalities such as Paralytic Ileus, PARKINSON DISEASE, LATE-ONSET, Fibrillation, Hepatic necrosis and Lymphopenia. The involved functions are known as Atrophic, Ulcer, Necrosis, Apoptosis and antagonists. Gossypol often locates in Mucous Membrane, Epithelium, Blood, Microsomes, Liver and Autophagic vacuole. The associated genes with Gossypol are BCL2A1 gene, BCL2 gene, Transgenes, IGH@ gene cluster and Bax protein (53-86). The related lipids are Promega, proteoliposomes, Phosphatidylserines and Liposomes. The related experimental models are Transgenic Model and Xenograft Model.

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Introduction

To understand associated biological information of Gossypol, we collected biological information of abnormalities, associated pathways, cellular/molecular locations, biological functions, related genes/proteins, lipids and common seen animal/experimental models with organized paragraphs from literatures.

What diseases are associated with Gossypol?

Gossypol is suspected in Severe Combined Immunodeficiency, Aortic Valve Insufficiency, PARKINSON DISEASE, LATE-ONSET, Infertility, CLEFT LIP, CONGENITAL HEALED, Pulmonary Fibrosis and other diseases in descending order of the highest number of associated sentences.

Related references are mostly published in these journals:

Disease Cross reference Weighted score Related literature
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Possible diseases from mapped MeSH terms on references

We collected disease MeSH terms mapped to the references associated with Gossypol

MeSH term MeSH ID Detail
Hemolysis D006461 131 associated lipids
Neovascularization, Pathologic D009389 39 associated lipids
Adenocarcinoma D000230 166 associated lipids
Lung Neoplasms D008175 171 associated lipids
Pancreatic Neoplasms D010190 77 associated lipids
Colonic Neoplasms D003110 161 associated lipids
Cattle Diseases D002418 24 associated lipids
Infertility, Male D007248 11 associated lipids
Mammary Neoplasms, Experimental D008325 67 associated lipids
Body Weight D001835 333 associated lipids
Per page 10 20 50 100 | Total 52

PubChem Associated disorders and diseases

What pathways are associated with Gossypol

Lipid pathways are not clear in current pathway databases. We organized associated pathways with Gossypol through full-text articles, including metabolic pathways or pathways of biological mechanisms.

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Pathway name Related literatures
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PubChem Biomolecular Interactions and Pathways

Link to PubChem Biomolecular Interactions and Pathways

What cellular locations are associated with Gossypol?

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Location Cross reference Weighted score Related literatures
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What functions are associated with Gossypol?


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Function Cross reference Weighted score Related literatures

What lipids are associated with Gossypol?

Related references are published most in these journals:

Lipid concept Cross reference Weighted score Related literatures
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What genes are associated with Gossypol?

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Gene Cross reference Weighted score Related literatures

What common seen animal models are associated with Gossypol?

Xenograft Model

Xenograft Model are used in the study 'Gossypol induces apoptosis by activating p53 in prostate cancer cells and prostate tumor-initiating cells.' (Volate SR et al., 2010), Xenograft Model are used in the study 'Sorafenib sensitizes (-)-gossypol-induced growth suppression in androgen-independent prostate cancer cells via Mcl-1 inhibition and Bak activation.' (Lian J et al., 2012), Xenograft Model are used in the study 'Natural BH3 mimetic (-)-gossypol chemosensitizes human prostate cancer via Bcl-xL inhibition accompanied by increase of Puma and Noxa.' (Meng Y et al., 2008), Xenograft Model are used in the study '(-)-Gossypol suppresses the growth of human prostate cancer xenografts via modulating VEGF signaling-mediated angiogenesis.' (Pang X et al., 2011) and Xenograft Model are used in the study 'Gossypol induces death receptor-5 through activation of the ROS-ERK-CHOP pathway and sensitizes colon cancer cells to TRAIL.' (Sung B et al., 2010).

Transgenic Model

Transgenic Model are used in the study 'Bcl-2 antagonist apogossypol (NSC736630) displays single-agent activity in Bcl-2-transgenic mice and has superior efficacy with less toxicity compared with gossypol (NSC19048).' (Kitada S et al., 2008).

Related references are published most in these journals:

Model Cross reference Weighted score Related literatures
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NCBI Entrez Crosslinks

All references with Gossypol

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Per page 10 20 50 100 | Total 1511
Authors Title Published Journal PubMed Link
Kennedy WP et al. Gossypol inhibition of acrosin and proacrosin, and oocyte penetration by human spermatozoa. 1983 Biol. Reprod. pmid:6416323
Shandilya L et al. Effects of gossypol on reproductive and endocrine functions of male cynomolgus monkeys (Macaca fascicularis). 1982 Biol. Reprod. pmid:7115850
Dabrowski K et al. Effects of diets containing gossypol on reproductive capacity of rainbow trout (Oncorhynchus mykiss). 2000 Biol. Reprod. pmid:10642557
Hoffer AP et al. Ultrastructural, fertility, and spermicidal studies with isomers and derivatives of gossypol in male hamsters. 1987 Biol. Reprod. pmid:3689857
Tanphaichitr N et al. Direct effect of gossypol on TR-ST cells: perturbation of rhodamine 123 accumulation in mitochondria. 1984 Biol. Reprod. pmid:6518226
Shi QX and Friend DS Gossypol-induced inhibition of guinea pig sperm capacitation in vitro. 1983 Biol. Reprod. pmid:6640034
Olgiati KL et al. Gossypol modulation of nucleotide metabolizing enzymes in the reproductive tract of male rats. 1984 Biol. Reprod. pmid:6095938
Hoffer AP and Hinton BT Morphological evidence for a blood-epididymis barrier and the effects of gossypol on its integrity. 1984 Biol. Reprod. pmid:6733204
Oko R and Hrudka F Comparison of the effects of gossypol, estradiol-17 beta and testosterone compensation on male rat reproductive organs. 1984 Biol. Reprod. pmid:6733210
Hoffer AP Effects of gossypol on the seminiferous epithelium in the rat: a light and electron microscope study. 1983 Biol. Reprod. pmid:6860736
Santana AT et al. Mechanisms involved in reproductive damage caused by gossypol in rats and protective effects of vitamin E. 2015 Biol. Res. pmid:26227499
Gu ZW et al. Studies on fertility control-the formation and antifertility effect of polyvinyl-pyrolidone-gossypol complex. 1984 Biomater Med Devices Artif Organs pmid:6532483
Li K et al. Mulberry-like dual-drug complicated nanocarriers assembled with apogossypolone amphiphilic starch micelles and doxorubicin hyaluronic acid nanoparticles for tumor combination and targeted therapy. 2015 Biomaterials pmid:25477180
Zhang H et al. Canonical Wnt signaling acts synergistically on BMP9-induced osteo/odontoblastic differentiation of stem cells of dental apical papilla (SCAPs). 2015 Biomaterials pmid:25468367
Xu R et al. Proteomic analysis of gossypol induces necrosis in multiple myeloma cells. 2014 Biomed Res Int pmid:25197664
Jin L et al. Phosphoproteomic analysis of gossypol-induced apoptosis in ovarian cancer cell line, HOC1a. 2014 Biomed Res Int pmid:25180175
Gong Y et al. Valproic Acid Enhances the Anti-tumor Effect of (-)-gossypol to Burkitt Lymphoma Namalwa Cells. 2015 Biomed. Environ. Sci. pmid:26582100
Xin J et al. ApoG2 as the most potent gossypol derivatives inhibits cell growth and induces apoptosis on gastric cancer cells. 2013 Biomed. Pharmacother. pmid:23201009
Tiliabaev KZ et al. [Synthesis, structures, and acute toxicity of gossypol nonsymmetrical aldehyde derivatives]. 2010 May-Jun Bioorg. Khim. pmid:20644599
Dao VT et al. New thioderivatives of gossypol and gossypolone, as prodrugs of cytotoxic agents. 2003 Bioorg. Med. Chem. pmid:12670651
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Xing C et al. Development of selective inhibitors for anti-apoptotic Bcl-2 proteins from BHI-1. 2007 Bioorg. Med. Chem. pmid:17227711
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Przybylski P et al. Antifungal activity of alkyl and heterocyclic aza-derivatives of gossypol as well as their complexes with NaClO4 against Fusarium oxysporum f. sp. lupini. 2009 Bioorg. Med. Chem. Lett. pmid:19264482
Janssen CO et al. Interaction of kendomycin and semi-synthetic analogues with the anti-apoptotic protein Bcl-xl. 2008 Bioorg. Med. Chem. Lett. pmid:18845435
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Yang J et al. Synthesis and anti-H5N1 activity of chiral gossypol derivatives and its analogs implicated by a viral entry blocking mechanism. 2013 Bioorg. Med. Chem. Lett. pmid:23538114
Wu Y et al. Changes in membrane properties during energy depletion-induced cell injury studied with fluorescence microscopy. 1996 Biophys. J. pmid:8804592
Przybylski P et al. Spectroscopic studies and PM5 semiempirical calculations of new Schiff bases of gossypol with polyoxaalkylamines. 2002 Biopolymers pmid:12209461
Przybylski P et al. Schiff base of gossypol with 3,6,9-trioxa-decylamine complexes with monovalent cations studied by mass spectrometry, (1)H-NMR, FTIR, and PM5 semiempirical methods. 2004 Biopolymers pmid:14991665
Przybylski P et al. 1H- and 13C-NMR, FTIR, UV-VIS, ESI-MS, and PM5 studies as well as emission properties of a new Schiff base of gossypol with 5-methoxytryptamine and a new hydrazone of gossypol with dansylhydrazine. 2006 Biopolymers pmid:16538663
Przybylski P et al. Multinuclear magnetic resonance, electrospray ionization-mass spectroscopy, and parametric method 5 studies of a new derivative of gossypol with 2-thiophenecarbohydrazide as well as its complexes with LI+, Na+, K+, RB+, and Cs+ cations. 2006 Biopolymers pmid:16741985
Przybylski P et al. The schiff base of gossypol with 3,6,9,12,15,18,21,24-octaoxa-pentacosylamine complexes and monovalent cations studied by electrospray ionization-mass spectrometry, (1)H nuclear magnetic resonance, Fourier transform infrared, as well as PM5 semiempirical methods. 2004 Biopolymers pmid:15211497
Przybylski P and Brzezinski B Spectroscopic studies and PM3 semiempirical calculations of Schiff bases of gossypol with L-amino acid methyl esters. 2002 Biopolymers pmid:11842415
Shibatani M et al. Accumulation of Isohemigossypolone and Its Related Compounds in the Inner Bark and Heartwood of Diseased Pachira aquatica. 1999 Biosci. Biotechnol. Biochem. pmid:26300168
Sagach VF and Kindybaliuk AM [The role of the endothelium in the development of functional hyperemia of the skeletal muscles]. 1991 Biull Eksp Biol Med pmid:1810472
Sonpavde G et al. Radiographic progression by Prostate Cancer Working Group (PCWG)-2 criteria as an intermediate endpoint for drug development in metastatic castration-resistant prostate cancer. 2014 BJU Int. pmid:24298897
Kitada S et al. Bcl-2 antagonist apogossypol (NSC736630) displays single-agent activity in Bcl-2-transgenic mice and has superior efficacy with less toxicity compared with gossypol (NSC19048). 2008 Blood pmid:18202226
Paoluzzi L et al. Targeting Bcl-2 family members with the BH3 mimetic AT-101 markedly enhances the therapeutic effects of chemotherapeutic agents in in vitro and in vivo models of B-cell lymphoma. 2008 Blood pmid:18292288
Balakrishnan K et al. Gossypol, a BH3 mimetic, induces apoptosis in chronic lymphocytic leukemia cells. 2008 Blood pmid:18566329
Balakrishnan K et al. AT-101 induces apoptosis in CLL B cells and overcomes stromal cell-mediated Mcl-1 induction and drug resistance. 2009 Blood pmid:18836097
Pan R et al. Inhibition of Mcl-1 with the pan-Bcl-2 family inhibitor (-)BI97D6 overcomes ABT-737 resistance in acute myeloid leukemia. 2015 Blood pmid:26045609
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Zhao R et al. AT-101 enhances gefitinib sensitivity in non-small cell lung cancer with EGFR T790M mutations. 2016 BMC Cancer pmid:27431492
Mani J et al. Chemoresistance is associated with increased cytoprotective autophagy and diminished apoptosis in bladder cancer cells treated with the BH3 mimetic (-)-Gossypol (AT-101). 2015 BMC Cancer pmid:25885284
Celorio-Mancera Mde L et al. Transcriptional responses underlying the hormetic and detrimental effects of the plant secondary metabolite gossypol on the generalist herbivore Helicoverpa armigera. 2011 BMC Genomics pmid:22111916
Wang J et al. Reversal of a full-length mutant huntingtin neuronal cell phenotype by chemical inhibitors of polyglutamine-mediated aggregation. 2005 BMC Neurosci pmid:15649316